Not sure if there is anyone out there that hasn’t yet found a fix?
…but I found one!!!!
THE BLAH BLAH BLAH…
I tried many different suggested ways of getting my phone to sync music.
I kept clicking on songs i wanted to listen to on my iphone, and it would just zoom through my lists playlists and only play 'itunes purchased’ music and leave all other music greyed out and/or with a small red square inside a circle.
After weeks of fuming about how crappy and stupid apple is becoming... and scrolling through lots of posts on how to fix it and this is what worked, instantly, with bugger all effort/time/syncing.
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THE SOLOUTION
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go to 'Music' button on your device... (in my case iphone 5).
Make sure your phone is on the inital screen, where down the bottom, it has 5 sub options...
-Radio
-Playlists
-Artists
-Songs
-More
"More" is what you are after... so click/navigate to "More", then go down to the "Shared" option.
there were two options listed under the 'Shared Tab' within 'Music' on my iphone;
Ashley's iPhone
and
Ashley's Library
My phone was set to "Ashley's iPhone" - (there was a tick next to this option)
I instead selected and changed my shared setting to ; "Ashley's Library"
And it worked. INSTANTLY. Smple as that.
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(please note; not sure if it makes any difference, but fyi my phone is using ios 7.0.6. )
Well this has been my first post, ever. And I REALLY hope this works for anyone still having this infuriating issue... life with out tunes is agony (it was for me). Hence this post.
GOOD LUCK!